Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
The present application claims priority to the application, 63/369,475, with the effective filing dates of 26 July 2022.
Claim Status
This Office Action is in response to Applicant’s Response to Restriction filed, 22 May 2026.
Applicant’s election without traverse of Group II (claims 10-20) in the reply filed 22 May 2026 is acknowledged.
Claims 1-9 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group (Group I: 1-9), there being no allowable generic or linking claim.
Claims 10-20 are under consideration in the instant office action.
Information Disclosure Statement
The Information Disclosure Statement filed on 15 Jan 2025 and the references cited therein have been considered, unless indicated otherwise.
Claim Interpretation
For purposes of clarity, the Examiner notes that claim 10 recites the limitation “the electron-donor-acceptor complex absorbs blue light,” which is a property and that claim 12 recites the limitation “irradiating the electron-donor-acceptor complex with light having a wavelength of between 400 nm and 500 nm.” Claim 10 specifies a property of the electron-donor-acceptor complex, and claim 12 further recites an additional step (irradiating) and is thus further limiting.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
1. Claim 12 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 12 recites a wavelength of between about 400 nm and 500 nm. However, the specification defines the term “about” to mean values near to a recited value ([0044]) and further elaborates that “about” can mean within ± 25%, ± 20%, ± 15%, ± 10%, ± 9%, ± 8%, ± 7%, ± 6%, ± 5%, ± 4%, ± 3%, ± 2%, ± 1%, less than ± 1%, or any other value or range of values therein ([0044]). Accordingly, about 25% of 400 is ± 100, which is 300-500 nm, and about 25% of 500 is ± 125, which is 375-625 nm. Because the endpoints are no longer distinguishable and significantly overlap, the claimed invention is unclear as to what is or is not near to a recited value. Thus, one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Accordingly, it is ambiguous as to the exact range of wavelengths that Applicant considers part of the claimed invention and what degree of similarity would infringe.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
2. Claim(s) 10-20 are rejected under 35 U.S.C. 103 as being unpatentable over Dorsheimer (JACS¸2021, 143, 19294-19299, see IDS filed 15 Jan 2025) in view of Lu (Org. Lett.¸2021, 23, 5425-5429), Mao (ACIE¸2018, 57, 9501-9504), Liang (Nature¸2018, 559, 83-93), and Deev (RSC Adv., 2019, 9, 26856-26879).
Dorsheimer teaches activation of alpha-primary and -secondary amines via the redox-active Katritzky salts to form carbon-carbon bonds (Scheme 1, page 19294):
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. Dorsheimer additionally teaches that the same transformation for alpha-tertiary amines do not condense onto triphenyl-pyrylium salts like their alpha-primary and -secondary counterparts (Scheme 1B, page 19294; page 19294, column 1, paragraph 1). Further, Dorsheimer teaches the use of a photocatalyst in conjunction with a nickel catalyst to activate the carbon-nitrogen bond of alpha-tertiary amines via condensing onto an electron-rich aldehyde activating group (page 19294, column 1, paragraph 1; Scheme 1C, page 19294). Dorsheimer specifically utilizes the iridium photocatalyst:
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and a tetramethylheptanedionato (THMD) nickel(II) catalyst with blue light (specifically at the wavelength, 456 nm) to perform the transformation (page 19295, column 1, paragraph 2; page 19295, Table 1). Additionally, Dorsheimer teaches that the reaction proceeds through an electron-donor-acceptor complex (Scheme 3B, page 19297). Dorsheimer teaches that the aryl imine accepts an electron via single electron transfer and undergoes beta-scission to generate ArCN and the tertiary radical, which then interacts with the Ni(III) complex wherein the Ni(III) complex traps the tertiary radical and the alkylated product reductively eliminates to generate the Ni(II) species (Scheme 3B, page 19297).
Regarding claim 10, Dorsheimer fails to teach the 15N isotope, using a copper(I) catalyst, irradiating the electron-donor-acceptor complex, forming a Cu(II) species, exchanging a ligand of the Cu(II) species with a 15N-labeled benzophenone imine and trapping the primary or secondary radical to generate a Cu(III) species, and reductively eliminating from the Cu(III) species to close the copper catalysis cycle.
Lu teaches donor-acceptor complexes utilizing Katritzky salts (abstract). Lu teaches the cascade radical cyclization of N-arylacrylamides with simple and easily available alkyl radical precursors under mild and oxidant- and metal-free conditions (page 5425, column 2, paragraph 1). Lu teaches that there was a previously reported weak interaction of Katritzky salts and NaI which formed a photoactive electron-donor-acceptor complex for functionalizing alkenes (page 5426, column 1, paragraph 1). Lu teaches a deaminitive strategy for the cascade radical cyclization of N-arylacrylamides via Katritzky salts and that the solvent can significantly enhance the photoactivity of the electron-donor-acceptor complex (page 5427, column 2, paragraph 4).
Mao teaches cross-coupling of alkyl redox-active esters with benzophenone imines via photoredox and copper catalysis (abstract). Mao teaches that alkyl amines are prevalent in synthetic intermediates and bioactive molecules and that amine substitution is difficult or even impossible for bulky secondary and tertiary alkyl halides (page 9501, column 1, paragraph 1). Mao further teaches that elimination and overalkylation are common substitution pitfalls (page 9501, column 1, paragraph 1). Mao teaches that C(sp3)-N cross-coupling has the potential to overcome the shortcomings of direct substitution but that the coupling is also only in its infancy (page 9501, column 1, paragraph 1). Mao teaches that beta-hydride elimination from metal alkyl intermediates and difficulty in C(sp3)-N reductive elimination are two perceived problems (page 9501, column 1, paragraph 1). Mao then teaches that the issues associated with steric hindrance or difficulty in reductive elimination were successfully solved via using a benzophenone-derived imine nucleophile with an sp2-hybridized nitrogen center, which is more sterically accessible and more prone to reductive elimination:
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(page 9501, column 2, paragraphs 2-3; Figure 1, page 9501; page 9502, column 1, paragraph 2). Mao teaches coordination of the benzophenone imine with a low-valent copper catalyst followed by deprotonation to form the Cu(I) species, II (Figure 1, page 9501; page 9502, column 1, paragraph 2). Mao then teaches generation of the photo-excited complex which reduces the ester through single-electron transfer to afford the alkyl radical, which is then captured by species II to yield the Cu(II) complex, intermediate III (Figure 1, page 9501; page 9502, column 1, paragraph 2). Mao teaches that Intermediate III is oxidized to form the Cu(III) complex and the amine reductively eliminates to close the copper catalysis cycle (Figure 1, page 9501; page 9502, column 1, paragraph 2).
Liang teaches a carbon-nitrogen coupling protocol with high regioselectivity using substrates that contain several amine groups, which the application to complex drug molecules, enabling the rapid construction of molecule complexity and late-stage functionalization of bioactive pharmaceuticals (abstract). Liang teaches that the efficient construction of C-N bonds is important owing to the prevalence of nitrogen-containing motifs in a wide array of natural product, pharmaceuticals, and functional materials (page 83, column 1, paragraph 1). Liang teaches that sp3 C-N bond formation typically relies on nucleophilic substitution between nitrogen nucleophiles and alkyl halides, Mitsunobu alkylations of alkyl of alcohols using nitrogen nucleophiles, reductive amination with carbonyls, or olefin hydroamination (page 83, column 1, paragraph 1). Liang teaches that the combination of nickel and photoredox catalysis has enabled efficient construction of the C(sp3)-C(sp2) and C(sp3)-C(sp3) bonds from abundant alkyl carboxylic acids and alcohols (page 83, column 1, paragraph 2). However, Liang teaches copper catalysis in lieu of nickel, which enables alkyl sp3 C-N bond formation without the use of alkyl halides or other prototypical electrophiles (page 83, column 1, paragraph 2). Liang teaches coordination of the nitrogen nucleophile with the copper(I) precatalyst followed by deprotonation to form the copper(I) species, which then is oxidized via the excited iridium photocatalyst to generate the corresponding copper(II) species (page 83, column 2, paragraph 2; Figure 2a, page 84). Liang teaches then that the copper(II) species exchanges a ligand with the nucleophile and traps the alkyl radical (secondary radical in Figure 2a) to form the copper(III) complex, which undergoes reductive elimination to yield the sp3 C-N adduct (page 83, column 2, paragraph 2; Figure 2a, page 84).
Deev teaches that 15N labeling is a tool to study the structural aspects and pathways of chemical transformations (abstract). Deev teaches that nitrogen heterocycles are a ubiquitous class of organic compounds and that their accompanying structures are inherent in drug design and natural compounds, in catalysis for cross-coupling, and asymmetric synthesis reaction (page 26856, column 1, paragraph 1). Deev teaches that selective 15N-labeleing of organic molecules leads to the appearance of additional 1H-15N and 13C-15N spin-spin coupling constants that significantly expand the application of NMR methods in the determination of molecular structures (page 26856, column 2, paragraph 2). Deev teaches that incorporation of the 15N atom into structures leads to the appearance of isotope shifts (page 26856, column2, paragraph 3). Deev teaches that despite the great opportunities for selective 15N incorporation followed by analysis of the J couplings, no systematic review devoted to the structure studies of heterocycles has been previously presented and that Deev presents the first attempt to generalize the literature data on 15N-labeling and show the capacity of using J coupling data for the determination of molecular structure and chemical transformations of nitrogen-containing heterocycles (page 26857, column 1, paragraph 2).
It would have been obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention to modify the method of Dorsheimer to incorporate the copper catalysis of Mao and Liang to prepare 15N isotopes as taught by Deev to arrive at instant claim 10. One of ordinary skill in the art would have been motivated to make such a selection, with a reasonable expectation of success, because:
-Dorsheimer teaches activation of alpha-primary and -secondary amines via the redox-active Katritzky salts to form carbon-carbon bonds:
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,
-Dorsheimer teaches that the same transformation for alpha-tertiary amines do not condense onto triphenyl-pyrylium salts like their alpha-primary and -secondary counterparts,
-Dorsheimer teaches use of a photocatalyst in conjunction with a nickel catalyst to activate the carbon-nitrogen bond of alpha-tertiary amines via condensing onto an electron-rich aldehyde activating group,
-Dorsheimer specifically utilizes the iridium photocatalyst:
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and a tetramethylheptanedionato (THMD) nickel(II) catalyst with blue light (specifically at the wavelength, 456 nm) to perform the transformation,
-Dorsheimer teaches that the reaction proceeds through an electron-donor-acceptor complex,
-Dorsheimer teaches that the aryl imine accepts an electron via single electron transfer and undergoes beta-scission to generate ArCN and the tertiary radical, which then interacts with the Ni(III) complex wherein the Ni(III) complex traps the tertiary radical and the alkylated product reductively eliminates to generate the Ni(II) species,
-Lu teaches donor-acceptor complexes utilizing Katritzky salts (abstract). Lu teaches the cascade radical cyclization of N-arylacrylamides with simple and easily available alkyl radical precursors under mild and oxidant- and metal-free conditions,
-Lu teaches that there was a previously reported weak interaction of Katritzky salts and NaI which formed a photoactive electron-donor-acceptro complex for functionalizing alkenes,
-Lu teaches a deaminitive strategy for the cascade radical cyclization of N-arylacrylamides via Katritzky salts and that the solvent can significantly enhance the photoactivity of the electron-donor-acceptor complex,
-Mao teaches cross-coupling of alkyl redox-active esters with benzophenone imines via photoredox and copper catalysis,
-Mao teaches that alkyl amines are prevalent in synthetic intermediates and bioactive molecules and that amine substitution is difficult or even impossible for bulky secondary and tertiary alkyl halides,
-Mao further teaches that elimination and overalkylation are common substitution pitfalls,
-Mao teaches that C(sp3)-N cross-coupling has the potential to overcome the shortcomings of direct substitution but that the coupling is also only in its infancy,
-Mao teaches that beta-hydride elimination from metal alkyl intermediates and difficulty in C(sp3)-N reductive elimination are two perceived problems,
-Mao then teaches that the issues associated with steric hindrance or difficulty in reductive elimination were successfully solved via using a benzophenone-derived imine nucleophile with an sp2-hybridized nitrogen center, which is more sterically accessible and more prone to reductive elimination:
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,
-Mao teaches coordination of the benzophenone imine with a low-valent copper catalyst followed by deprotonation to form the Cu(I) species, II,
-Mao then teaches generation of the photo-excited complex which reduces the ester through single-electron transfer to afford the alkyl radical, which is then captured by species II to yield the Cu(II) complex, intermediate III,
-Mao teaches that Intermediate III is oxidized to form the Cu(III) complex and the amine reductively eliminates to close the copper catalysis cycle,
-Liang teaches a carbon-nitrogen coupling protocol with high regioselectivity using substrates that contain several amine groups, which the application to complex drug molecules, enabling the rapid construction of molecule complexity and late-stage functionalization of bioactive pharmaceuticals,
-Liang teaches that the efficient construction of C-N bonds is important owing to the prevalence of nitrogen-containing motifs in a wide array of natural product, pharmaceuticals, and functional materials,
-Liang teaches that sp3 C-N bond formation typically relies on nucleophilic substitution between nitrogen nucleophiles and alkyl halides, Mitsunobu alkylations of alkyl of alcohols using nitrogen nucleophiles, reductive amination with carbonyls, or olefin hydroamination,
-Liang teaches that the combination of nickel and photoredox catalysis has enabled efficient construction of the C(sp3)-C(sp2) and C(sp3)-C(sp3) bonds from abundant alkyl carboxylic acids and alcohols,
-Liang teaches copper catalysis in lieu of nickel, which enables alkyl sp3 C-N bond formation without the use of alkyl halides or other prototypical electrophiles,
-Liang teaches coordination of the nitrogen nucleophile with the copper(I) precatalyst followed by deprotonation to form the copper(I) species, which then is oxidized via the excited iridium photocatalyst to generate the corresponding copper(II) species,
- Liang teaches then that the copper(II) species exchanges a ligand with the nucleophile and traps the alkyl radical (secondary radical in Figure 2a) to form the copper(III) complex, which undergoes reductive elimination to yield the sp3 C-N adduct,
-Deev teaches that 15N labeling is a tool to study the structural aspects and pathways of chemical transformations,
-Deev teaches that nitrogen heterocycles are a ubiquitous class of organic compounds and that their accompanying structures are inherent in drug design and natural compounds, in catalysis for cross-coupling, and asymmetric synthesis reaction,
-Deev teaches that selective 15N-labeleing of organic molecules leads to the appearance of additional 1H-15N and 13C-15N spin-spin coupling constants that significantly expand the application of NMR methods in the determination of molecular structures,
-Deev teaches that incorporation of the 15N atom into structures leads to the appearance of isotope shifts, and
-Deev teaches that despite the great opportunities for selective 15N incorporation followed by analysis of the J couplings, no systematic review devoted to the structure studies of heterocycles has been previously presented and that Deev presents the first attempt to generalize the literature data on 15N-labeling and show the capacity of using J coupling data for the determination of molecular structure and chemical transformations of nitrogen-containing heterocycles.
Thus, the combination of Dorsheimer, Lu, Mao, Liang, and Deev teaches a method for producing 15-N-labeled compound having an alpha-primary amine or alpha-secondary amine comprising: condensing an alpha-primary amine or alpha-secondary amine with a pyrilium salt to generate a Katritzky pyridinium salt; mixing the Katritzky pyridinium salt and a copper(I) catalyst containing a 1,3-diketone ligand in the presence of a base to generate an electron-donor-acceptor complex, wherein the electron-donor-acceptor complex absorbs blue light; fragmenting the electron-donor-acceptor complex to generate a primary or secondary radical and a Cu(II) species; exchanging a ligand of the Cu(II) species with an 15N-labeled benzophenone imine and trapping the primary or secondary radical to generate a Cu(III) species; and generating the 15N-labeled compound having the alpha-primary amine or alpha-secondary amine by reductive elimination of the Cu(III) species.
Regarding claim 11, Liang teaches that the compound is a pharmaceutical compound (page 83, column 1, paragraph 1).
Regarding claim 12, Dorsheimer specifically utilizes the iridium photocatalyst:
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and a tetramethylheptanedionato (THMD) nickel(II) catalyst with blue light (specifically at the wavelength, 456 nm) to perform the transformation (page 19295, column 1, paragraph 2; page 19295, Table 1). Lu teaches that the electron-donor-acceptor complex is irradiated (page 5427, column 2, paragraph 4). Thus, the combination of Dorsheimer and Lu teaches that the electron-donor-acceptor complex is irradiated with light having a wavelength of between about 400 nm and 500nm.
Regarding claim 13, Dorsheimer teaches the light to irradiate is at the wavelength, 456 nm (page 19295, column 1, paragraph 2; page 19295, Table 1).
Regarding claim 14, Dorsheimer teaches the tetramethylheptanedionato (THMD) nickel(II) catalyst to perform the transformation (page 19295, column 1, paragraph 2; page 19295, Table 1).
Regarding claim 15, Mao teaches the base is cesium carbonate (page 9502, column 1, paragraph 3).
Regarding claim 16, Mao teaches the product of the C-N cross-coupling is
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(page 9205, Table 2). Additionally, Liang teaches
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(page 85, Figure 3). Deev teaches 15N labeling is a tool to study the structural aspects and pathways of chemical transformations (abstract). Further, Deev teaches that incorporation of the 15N atom into structures leads to the appearance of isotope shifts (page 26856, column2, paragraph 3). Thus, the combination of Mao, Liang, and Deev teaches the 15N-labeled compound
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and
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.
Regarding claim 17, Lu teaches production of indoles:
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(page 5426, Scheme 2). Deev teaches the 15N-labeling of isothiazole:
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(Scheme 21, page 26865) and imidazoles:
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(page 26865, Scheme 24). Thus, the combination of Lu and Deev teaches the 15N-labeled compound is an indole or an imidazole.
Regarding claim 18, Dorsheimer teaches activation of alpha-primary and -secondary amines via the redox-active Katritzky salts to form carbon-carbon bonds (Scheme 1, page 19294):
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. Dorsheimer teaches use of a photocatalyst in conjunction with a nickel catalyst to activate the carbon-nitrogen bond of alpha-tertiary amines via condensing onto an electron-rich aldehyde activating group (page 19294, column 1, paragraph 1; Scheme 1C, page 19294). Dorsheimer specifically utilizes the iridium photocatalyst:
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and a tetramethylheptanedionato (THMD) nickel(II) catalyst with blue light (specifically at the wavelength, 456 nm) to perform the transformation (page 19295, column 1, paragraph 2; page 19295, Table 1). Lu teaches electron-donor-acceptor complexes utilizing Katritzky salts (abstract). Mao teaches cross-coupling of alkyl redox-active esters with benzophenone imines via photoredox and copper catalysis (abstract). Mao teaches coordination of the benzophenone imine with a low-valent copper catalyst followed by deprotonation to form the Cu(I) species, II (Figure 1, page 9501; page 9502, column 1, paragraph 2). Mao then teaches generation of the photo-excited complex which reduces the ester through single-electron transfer to afford the alkyl radical, which is then captured by species II to yield the Cu(II) complex, intermediate III (Figure 1, page 9501; page 9502, column 1, paragraph 2). Mao teaches that Intermediate III is oxidized to form the Cu(III) complex and the amine reductively eliminates to close the copper catalysis cycle (Figure 1, page 9501; page 9502, column 1, paragraph 2). Liang teaches coordination of the nitrogen nucleophile with the copper(I) precatalyst followed by deprotonation to form the copper(I) species, which then is oxidized via the excited iridium photocatalyst to generate the corresponding copper(II) species (page 83, column 2, paragraph 2; Figure 2a, page 84). Liang teaches then that the copper(II) species traps the alkyl radical to form the copper(III) complex, which undergoes reductive elimination to yield the sp3 C-N adduct (page 83, column 2, paragraph 2; Figure 2a, page 84). Liang teaches then that the copper(II) species exchanges a ligand with the nucleophile and traps the alkyl radical (secondary radical in Figure 2a) to form the copper(III) complex, which undergoes reductive elimination to yield the sp3 C-N (page 83, column 2, paragraph 2; Figure 2a, page 84). Deev teaches that 15N labeling is a tool to study the structural aspects and pathways of chemical transformations (abstract). Deev teaches that incorporation of the 15N atom into structures leads to the appearance of isotope shifts (page 26856, column2, paragraph 3).
Regarding claim 19, Deev teaches use of 15N-ammonium chloride as a nucleophile (page 26866, column 2, paragraph 3; page 26866, Scheme 26).
Regarding claim 20, Mao teaches the base is cesium carbonate (page 9502, column 1, paragraph 3).
Conclusion
No claim is allowed.
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/MADELINE M. DEKARSKE/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
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